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Transcript
AP BIOLOGY STUDY GUIDE
Chapter 4
Carbon and the Molecular Diversity of Life
Overview: Carbon—The Backbone of Biological Molecules

Although cells are 70–95% water, the rest consists of mostly carbon-based compounds.

Carbon enters the biosphere when photosynthetic organisms use the sun’s energy to transform
CO2 into organic molecules, which are transferred to primary consumers.

Carbon accounts for the diversity of biological molecules, which has made possible the wide
variety of living things.

Proteins, DNA, carbohydrates, and other molecules that distinguish living matter from inorganic
material are all composed of carbon atoms bonded to each other and to atoms of other elements.
o
These other elements commonly include hydrogen (H), oxygen (O), nitrogen (N),
sulfur (S), and phosphorus (P).
Concept 4.1 Organic chemistry is the study of carbon compounds.

Organic chemistry focuses on organic compounds containing carbon.
o
Organic compounds can range from simple molecules, such as CH4, to complex
molecules such as proteins, which may have molecular masses greater than 100,000
daltons.
o
Most organic compounds contain hydrogen atoms.

The overall percentages of the major elements of life (C, H, O, N, S, and P) are quite uniform
from one organism to another.

Because of carbon’s versatility, these few elements can be combined to build an inexhaustible
variety of organic molecules.

Variations in organic molecules can distinguish even individuals of a single species.

The science of organic chemistry began with attempts to purify and improve the yield of
products obtained from organisms.
o
Initially, chemists learned to synthesize simple compounds in the laboratory but had
no success with more complex compounds.

The Swedish chemist Jons Jacob Berzelius was the first to make a distinction between organic
compounds that seemed to arise in only living organisms and inorganic compounds that were
found in the nonliving world.

Early organic chemists proposed vitalism, the belief that physical and chemical laws do not
apply to living things.
o
Support for vitalism waned as organic chemists learned to synthesize complex
organic compounds in the laboratory.
o
In the early 1800s, the German chemist Friedrich Wöhler and his students
synthesized urea from totally inorganic materials.
Lecture Outline for Campbell/Reece Biology, 8th Edition, © Pearson Education, Inc.
4-1

In 1953, Stanley Miller at the University of Chicago set up a laboratory simulation of possible
chemical conditions on the primitive Earth and demonstrated the spontaneous synthesis of
organic compounds.
o
The mixture of gases Miller created probably did not accurately represent the
atmosphere of the primitive Earth.
o
However, similar experiments using more accurate atmospheric conditions also led
to the formation of organic compounds.
o
Spontaneous synthesis of organic compounds may have been an early stage in the
origin of life on Earth.

Organic chemists finally rejected vitalism and embraced mechanism, the belief that the same
physical and chemical laws govern all natural phenomena, including the processes of life.

Organic chemistry was redefined as the study of carbon compounds, regardless of their origin.

o
Organisms produce the majority of organic compounds.
o
The laws of chemistry apply to both inorganic and organic compounds.
The foundation of organic chemistry is not a mysterious life force but rather the unique
versatility of carbon-based compounds.
Concept 4.2 Carbon atoms can form diverse molecules by bonding to four other
atoms.

A carbon atom has a total of 6 electrons: 2 in the first electron shell and 4 in the second shell.

Carbon has little tendency to form ionic bonds by losing or gaining 4 electrons to complete its
valence shell.

Carbon usually completes its valence shell by sharing electrons with other atoms in four covalent
bonds, which may include single and double bonds.

Carbon’s tetravalence makes large, complex molecules possible.
o
When a carbon atom forms covalent bonds with four other atoms, they are arranged
at the corners of an imaginary tetrahedron with bond angles of 109.5°.
o
In molecules with multiple carbon atoms, every carbon atom bonded to four other
atoms has a tetrahedral shape.
o
When two carbon atoms are joined by a double bond, all bonds around those
carbons are in the same plane and have a flat, three-dimensional structure.
o
The electron configuration of carbon enables it to form covalent bonds with many
different elements.

The valences of carbon and its partners can be viewed as the building code that governs the
architecture of organic molecules.

In carbon dioxide, one carbon atom forms two double bonds with two different oxygen atoms.
o

In the structural formula, O=C=O, each line represents a pair of shared electrons.
This arrangement completes the valence shells of all atoms in the molecule.
Although CO2 can be classified as either organic or inorganic, its importance to the living world
is clear: CO2 is the source of carbon for all organic molecules found in organisms.
o
CO2 is usually fixed into organic molecules by the process of photosynthesis.

Urea, CO(NH2)2, is another simple organic molecule in which each atom forms covalent bonds
to complete its valence shell.
Molecular diversity arises from variations in the carbon skeleton.

Carbon chains form the skeletons of most organic molecules.
o
Carbon skeletons vary in length and may be straight, branched, or arranged in closed
rings.
o
Carbon skeletons may include double bonds.
o
Atoms of other elements can be bonded to the atoms of the carbon skeleton.

Hydrocarbons are organic molecules that consist of only carbon and hydrogen atoms.

Hydrocarbons are the major component of petroleum, a fossil fuel that consists of the partially
decomposed remains of organisms that lived millions of years ago.

Fats are biological molecules that have long hydrocarbon tails attached to a nonhydrocarbon
component.

Petroleum and fat are hydrophobic compounds that cannot dissolve in water because of their
many nonpolar carbon-hydrogen bonds.

Hydrocarbons can undergo reactions that release a relatively large amount of energy.

Isomers are compounds that have the same molecular formula but different structures and,
therefore, different chemical properties.

Structural isomers have the same molecular formula but differ in the covalent arrangement of
atoms.
o

Structural isomers may also differ in the location of the double bonds.
Geometric isomers have the same covalent partnerships but differ in the spatial arrangement of
atoms around a carbon-carbon double bond.
o
The double bond does not allow the atoms to rotate freely around the bond axis.
o
The biochemistry of vision involves a light-induced change in the structure of
rhodopsin in the retina from one geometric isomer to another.

Enantiomers are molecules that are mirror images of each other.

Enantiomers are possible when four different atoms or groups of atoms are bonded to an
asymmetric carbon.

o
The four groups can be arranged in space in two different ways that are mirror
images of each other.
o
They are like left-handed and right-handed versions of the molecule.
o
Usually one is biologically active, while the other is inactive.
Even subtle structural differences in two enantiomers may have important functional significance
because of emergent properties from specific arrangements of atoms.
o
For example, one enantiomer of the drug thalidomide reduced morning sickness,
the desired effect, but the other isomer caused severe birth defects.
Concept 4.3 Characteristic chemical groups help determine how biological molecules
function.
Lecture Outline for Campbell/Reece Biology, 8th Edition, © Pearson Education, Inc.
4-3

The distinctive properties of an organic molecule depend not only on the arrangement of its
carbon skeleton but also on the chemical groups attached to that skeleton.

If we start with hydrocarbons as the simplest organic molecules, characteristic chemical groups
can replace one or more of the hydrogen atoms bonded to the carbon skeleton of a
hydrocarbon.

These chemical groups may be involved in chemical reactions or may contribute to the shape
and function of the organic molecule in a characteristic way, giving it unique properties.
o
As an example, the basic structure of testosterone (a male sex hormone) and
estradiol (a female sex hormone) is the same.
o
Both are steroids with four fused carbon rings, but the hormones differ in the
chemical groups attached to the rings.
o
As a result, testosterone and estradiol have different shapes, causing them to interact
differently with many targets throughout the body.

In other cases, chemical groups known as functional groups affect molecular function through
their direct involvement in chemical reactions.

Seven chemical groups are most important to the chemistry of life: hydroxyl, carbonyl, carboxyl,
amino, sulfhydryl, phosphate, and methyl groups.

The first six chemical groups are functional groups. They are hydrophilic and increase the
solubility of organic compounds in water.

Methyl groups are not reactive but may serve as important markers on organic molecules.

In a hydroxyl group (—OH), a hydrogen atom forms a polar covalent bond with an oxygen
atom, which forms a polar covalent bond to the carbon skeleton.



o
Because of these polar covalent bonds, hydroxyl groups increase the solubility of
organic molecules.
o
Organic compounds with hydroxyl groups are alcohols, and their names typically
end in -ol.
A carbonyl group (>CO) consists of an oxygen atom joined to the carbon skeleton by a double
bond.
o
If the carbonyl group is on the end of the skeleton, the compound is an aldehyde.
o
If the carbonyl group is within the carbon skeleton, the compound is a ketone.
o
Isomers with aldehydes and those with ketones have different properties.
A carboxyl group (—COOH) consists of a carbon atom with a double bond to an oxygen atom
and a single bond to the oxygen atom of a hydroxyl group.
o
Compounds with carboxyl groups are carboxylic acids.
o
A carboxyl group acts as an acid because the combined electronegativities of the
two adjacent oxygen atoms increase the chance of dissociation of hydrogen as an
ion (H+).
An amino group (—NH2) consists of a nitrogen atom bonded to two hydrogen atoms and the
carbon skeleton.
o
Organic compounds with amino groups are amines.
o
The amino group acts as a base because it can pick up a hydrogen ion (H+) from the
solution.
o


Amino acids, the building blocks of proteins, have amino and carboxyl groups.
A sulfhydryl group (—SH) consists of a sulfur atom bonded to a hydrogen atom and to the
backbone.
o
This group resembles a hydroxyl group in shape.
o
Organic molecules with sulfhydryl groups are thiols.
o
Two sulfhydryl groups can interact to help stabilize the structure of proteins.
A phosphate group (—OPO32−) consists of a phosphorus atom bound to four oxygen atoms
(three with single bonds and one with a double bond).
o
A phosphate group connects to the carbon backbone via one of its oxygen atoms.
o
Phosphate groups are anions with two negative charges because 2 protons dissociate
from the oxygen atoms.
o
One function of phosphate groups is to transfer energy between organic molecules.
ATP is an important source of energy for cellular processes.

Adenosine triphosphate, or ATP, is the primary energy transfer molecule in living cells.

ATP consists of an organic molecule called adenosine attached to a string of three phosphate
groups.

When one inorganic phosphate ion is split off as a result of a reaction with water, ATP becomes
adenosine diphosphate, or ADP.
In a sense, ATP “stores” the potential to react with water, releasing energy that can be used by the
cell.
KEY TERMS: (1) Arrange the terms in the order in which they appear in the text and (2)
define each term.
Adenosine triphosphate
Enantiomer
Isomer
(ATP)
Amino group
Functional group
Organic chemistry
Carbonyl group
Geometric isomer
Phosphate group
Carboxyl group
Hydrocarbon
Structural isomer
Hydroxyl group
Sulfhydryl group
Lecture Outline for Campbell/Reece Biology, 8th Edition, © Pearson Education, Inc.
4-5